Title: Summerland Key Vacation Home Rentals from CA $573: Search Top Private Vacation Homes for Rent | Expedia.ca

 

[Summerland Key Travel Guide](https://expedia.ca/Summerland-Key.dx6177802)[Hotels in Summerland Key](https://expedia.ca/Summerland-Key-Hotels.d6177802.Travel-Guide-Hotels)[Vacation Rentals in Summerland Key](https://expedia.ca/Summerland-Key-Vacation-Rentals.d6177802.Travel-Guide-VacationRentals)[Flights to Summerland Key](https://expedia.ca/Cheap-Flights-To-Summerland-Key.d6177802.Travel-Guide-Flights)[Things to do in Summerland Key](https://expedia.ca/Things-To-Do-In-Summerland-Key.d6177802.Travel-Guide-Activities)[Summerland Key Car Rentals](https://expedia.ca/Car-Rentals-In-Summerland-Key.d6177802.Car-Rental-Guide)[Summerland Key Vacation Packages](https://expedia.ca/Summerland-Key.d6177802.Destination-Travel-Guides)

![Aerial view of road to Key West with turquoise water and small island, Summerland Key, Florida, United States.](https://images.trvl-media.com/place/6177802/f131c6a4-614b-4692-9e06-db0aca0a1329.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Summerland Key Vacation Rentals

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## Check prices for these dates

Next weekend

[Dec 5 - Dec 7](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-12-05&endDate=2025-12-07&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two weeks

[Dec 12 - Dec 14](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-12-12&endDate=2025-12-14&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In one month

[Dec 26 - Dec 28](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2025-12-26&endDate=2025-12-28&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Jan 23 - Jan 25](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2026-01-23&endDate=2026-01-25&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Browse Select Summerland Key Vacation Homes

![Outdoor dining](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/9c267ac9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/d57de0d1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/w1024h630x0y0-e267420a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/f2ffe64a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DECEMBER SAVE 50% OFF! WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

Cudjoe Key

9.6/10

Exceptional

(100)

"Great location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Davian k.

CA $236

CA $641 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Waterfront-Paradise-AT-Venture-Out4-Bikes-2-2-Seat-Kayaks-King-Queen-Beds.h32660303.Hotel-Information)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/93e2a835.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/f9199920.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/dbc7418b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/ab69be49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Starlight Serenity - Hideaway w Stunning Views

Summerland Key

CA $309

CA $815 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111872953.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/28679789.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/7f597dff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/8e7ed1a2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/45000000/44560000/44556700/44556643/6bfc69e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### DECEMBER SAVE 50% OFF OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS!

Cudjoe Key

9.8/10

Exceptional

(82)

"The place is clean and convenient for anyone wanting to spend time on the water in the keys"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Ubaldo G.

CA $348

CA $782 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Ocean-Paradise-AT-Venture-OUT-4-Bikes-2-2-Person-Kayaks.h44556643.Hotel-Information)

![Exterior detail](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/50d75af0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, WiFi, bed sheets](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/b22a7d78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/a4dfc6ce.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Microwave, oven, stovetop](https://images.trvl-media.com/lodging/118000000/117680000/117678200/117678152/bb5499e0.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key

Cudjoe Key

10/10

Exceptional

(2)

"Absolutely love it here… Randy is great to work with and always available. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jeannine R.

CA $270

CA $573 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Summerland-Key-Hotels-Charming-2-Bedroom-House-With-WiFi.h117678152.Hotel-Information)

![Balcony](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/0c89d58b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/3835dc3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/e93bd5d2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33550000/33547900/33547859/b25eb073.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Just 20 miles from Key West! Oceanfront, dockage, swimming pool

Cutthroat Harbor Estates

8.4/10

Very good

(118)

"Great experience "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Peyton S.

CA $314

CA $749 total

includes taxes & fees

Dec 6 - Dec 7

[](https://www.expedia.ca/Summerland-Key-Hotels-Just-20-Miles-From-Key-West-Oceanfront.h33547859.Hotel-Information)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/78d41425.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/2fb13370.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/611ec5f5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Smart TV, books](https://images.trvl-media.com/lodging/85000000/84050000/84046300/84046253/359e6f94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Kelly's Kabin - Adorable Private Summerland Key Cottage

Summerland Key

9.8/10

Exceptional

(121)

"We enjoyed our stay! Great little house and location. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lisa K.

CA $314

CA $760 total

includes taxes & fees

Dec 17 - Dec 18

[](https://www.expedia.ca/Summerland-Key-Hotels-Kellys-Kabin-Adorable-Private-Summerland-Key-Cottage.h84046253.Hotel-Information)

![Exterior](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/593a3590.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/3c80dd2a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/b3730c94.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![1 bedroom, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/ee0f875e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Starlight Serenity - Hideaway with Stunning Views

Summerland Key

CA $245

CA $793 total

includes taxes & fees

Dec 3 - Dec 4

[](https://www.expedia.ca/Summerland-Key-Hotels-Starlight-Serenity-Hideaway-W-Stunning-Views.h111873736.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/73acf8f1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/22584e28.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/f620b37f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/109000000/108500000/108496400/108496393/bea2cf35.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Island Time #110 Ocean Views - Cudjoe Key

Cudjoe Key

9.6/10

Exceptional

(11)

"Our family had an amazing vacation! We love the house and hope to come back!! "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Tammy G.

CA $294

CA $866 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Summerland-Key-Hotels-Island-Time-110-Ocean-Views-Cudjoe-Key.h108496393.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/ccda6a72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/09f11ae8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/af234045.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/117000000/116670000/116667100/116667062/d1b5e430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access

Cudjoe Key

CA $242

CA $801 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Summerland-Key-Hotels-Planktons-Palace-Cozy-2BR-Getaway-In-Oceanfront-Resort-Community-With-Patio-Island-Vibes.h116667062.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/119000000/118660000/118656100/118656049/c01d0a3a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/119000000/118660000/118656100/118656049/w2500h1666x0y1-475cf754.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/119000000/118660000/118656100/118656049/c518e45b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/119000000/118660000/118656100/118656049/w2499h1666x1y1-6b986066.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Galleon Getaway #533- Oceanfront Community

Cudjoe Key

CA $205

CA $757 total

includes taxes & fees

Dec 2 - Dec 3

[](https://www.expedia.ca/Summerland-Key-Hotels-Galleon-Getaway-533-Oceanfront-Community.h118656049.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/2f0f66a7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/87ae302c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach nearby](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/8a4fe85c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/a7e2aa66.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### The Hemingway - Beach Houses Key West

Upper Sugarloaf Key

9.8/10

Exceptional

(7)

"Perfect location way off the path if you like seclusion."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Jonathan L.

CA $1,991

CA $3,312 total

includes taxes & fees

Dec 24 - Dec 25

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-Bungalows-At-Sugarloaf-Beach-The-Hemingway.h77064022.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/a0a288d4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, table tennis, books](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/54d787f9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/96aae30a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/107000000/106920000/106911800/106911727/62b4ca8d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Salty Breeze #161 - Canal Front Venture Out Home on Cudjoe Key

Cudjoe Key

9.0/10

Wonderful

(7)

"Great place! Perfect location"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Troy B.

CA $330

CA $911 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Summerland-Key-Hotels-Salty-Breeze-161-Canal-Front-Venture-Out-Home-On-Cudjoe-Key.h106911727.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/e0161319.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, oven, stovetop, dishwasher](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/f6a09985.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/c295ed72.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/91000000/90020000/90010100/90010009/9443bf1a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Spanish Queen @Venture Out, Cudjoe Key

Cudjoe Key

9.4/10

Exceptional

(19)

"This is our third time staying here. It is a great property and works perfectly for a three-person family."

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Kimberly G.

CA $489

CA $951 total

includes taxes & fees

Dec 1 - Dec 2

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Spanish-Queen-Venture-Out.h90010009.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/9d72c172.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/40a49494.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/w2500h1666x0y1-ef4cfe80.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/121000000/120820000/120816900/120816897/30527523.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West

Cudjoe Key

CA $257

CA $821 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Summerland-Key-Hotels-Updated-2BR2BA-Venture-Out-Home-W-Pool-Access.h120816897.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/2af28832.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/30237e95.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/ef9badd3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310572/48816b03.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort

Cudjoe Key

CA $294

CA $868 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Summerland-Key-Hotels-Florida-Keys-Canal-Front-2BR2BA-W-35-Seawall.h121310572.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/4480719e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/b5098a17.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/94e8538a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/b38fa56b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Reel Island Retreat #273 at Venture Out in the Florida Keys

Cudjoe Key

9.6/10

Exceptional

(7)

"We really enjoyed our stay here. We really loved sitting on the back porch by the water and the closeness to the community pool and courts. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Lindsay C.

CA $294

CA $866 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Summerland-Key-Hotels-Reel-Island-Retreat-273-At-Venture-Out-In-The-Florida-Keys.h109794896.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/51bad23a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/80c5c4f7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/37c753b4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/7f2df60c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Waterfront 2BR/2BA with 35' Dock, Bikes & Kayaks – Island Breeze Keys Escape

Cudjoe Key

CA $294

CA $854 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Summerland-Key-Hotels-Waterfront-2BR2BA-With-35-Dock.h121310574.Hotel-Information)

![Outdoor pool](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/ccc6991c.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/4b59c6b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Children's area](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/c3e9677e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![4 bedrooms, iron/ironing board, free WiFi, bed sheets](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/996d51b7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### One of the very few beach houses with a daily, rental license in the Keys.

Summerland Key

8.8/10

Excellent

(65)

"My family and I had an incredible stay. We utilized every available component of the home including the dock. Property manager provided us with 2 available free ramps to drop off our jet-skis. We settled on the ramp located on Blimp Road, which was a 10 minute drive and 15-20 minute ride on the skis. We were able to tie off our skis our whole stay with no issues. Home was exactly as disclosed and worked great for our family. Communication was great, with quick respond time. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Yissel W.

CA $837

CA $1,942 total

includes taxes & fees

Dec 15 - Dec 16

[](https://www.expedia.ca/Summerland-Key-Hotels-Acreage-Beach-House-W-Pool-Billiards.h38413504.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/9e50721e.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/w2500h1666x0y1-6df08e77.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/3903b768.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89090000/89085000/89084949/39025159.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Relax at Keys Time – 2BR Waterfront Rental w/ Kayaks, Bikes, and Boat Dock

Cudjoe Key

9.4/10

Exceptional

(27)

"Close to Key West and lots of great boating"

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Simon S.

CA $404

CA $1,002 total

includes taxes & fees

Dec 4 - Dec 5

[](https://www.expedia.ca/Summerland-Key-Hotels-Relax-At-Keys-Time-2BR-Waterfront-Rental-W-Kayaks.h89084949.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/114000000/113460000/113458500/113458491/2a96627a.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/114000000/113460000/113458500/113458491/w2499h1562x1y1-92d1fa50.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/114000000/113460000/113458500/113458491/dd398ab3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/114000000/113460000/113458500/113458491/7a869856.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mahi House #440 - 35' seawall

Cudjoe Key

10/10

Exceptional

(1)

"The house was just right. Nice community. Quiet and peaceful. Just what we needed. The host was kind and responsive. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Emily P.

CA $295

CA $869 total

includes taxes & fees

Nov 30 - Dec 1

[](https://www.expedia.ca/Summerland-Key-Hotels-Mahi-House-440-35-Seawall.h113458491.Hotel-Information)

Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

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![](https://forever.travel-assets.com/flex/flexmanager/images/2025/11/05/BEX-BF-25_CA_1_Desktop.jpg?impolicy=fcrop&w=1400&h=600&q=mediumHigh)

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Apartments

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Cabins

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Cottages

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Houseboats

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## Top Summerland Key Hotel Reviews

![Parmer's Resort](https://images.trvl-media.com/lodging/6000000/5570000/5561500/5561465/6492712a_y.jpg)

### Parmer's Resort

10/10 Excellent

"We had a wonderful stay at Parmer's Resort. It was quiet and comfortable. We especially loved all the outdoor areas to sit and enjoy the views. "

[](https://expedia.ca/Little-Torch-Key-Hotels-Parmers-Resort.h5561465.Hotel-Information)

![Private Secluded Ocean View & Pool Near Key West](https://images.trvl-media.com/lodging/58000000/57870000/57865200/57865163/6b4e7932_y.jpg)

### Private Secluded Ocean View & Pool Near Key West

10/10 Excellent

"A wonderful time was had by all. Host was very responsive and we had no issues. Beautiful home and views!"

[](https://expedia.ca/Summerland-Key-Hotels-Private-Secluded-Ocean-View-Pool-Near-Key-West.h57865163.Hotel-Information)

![Sugarloaf Key Hotel at KOA Resort](https://images.trvl-media.com/lodging/102000000/101140000/101135800/101135765/3a7e709a_y.jpg)

### Sugarloaf Key Hotel at KOA Resort

10/10 Excellent

"The staff was great! At one point, we couldn’t get our washing machine started, only because of our error, and we had three people at our door, trying to help before we even got back to our room! Office staff always had a smile on their face! Beautiful park!"

[](https://expedia.ca/Sugarloaf-Key-Hotels-Sugarloaf-Key-Hotel.h101135765.Hotel-Information)

![Cottage with swimming pool and dockage, just minutes to Key West!](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/49b733bd_y.jpg)

### Cottage with swimming pool and dockage, just minutes to Key West!

10/10 Excellent

"Everything was there that I needed. Very nice area for my dog."

[](https://expedia.ca/Summerland-Key-Hotels-Cottage-With-Swimming-Pool-And-Dockage.h33566283.Hotel-Information)

![Relax by Florida Keys Beaches, just a 7-min drive away](https://images.trvl-media.com/lodging/35000000/34330000/34324000/34323967/504ad77a_y.jpg)

### Relax by Florida Keys Beaches, just a 7-min drive away

10/10 Excellent

"The cottage was clean and the location was nice and quiet. "

[](https://expedia.ca/Cudjoe-Key-Hotels-Waterfront-Fresh-Cozy-2-Bedroom-35seawall.h34323967.Hotel-Information)

![Looe Key Reef Resort](https://images.trvl-media.com/lodging/5000000/4760000/4759500/4759500/63d12f01_y.jpg)

### Looe Key Reef Resort

10/10 Excellent

"Lovely receptionist, very frieindly and helpful. Room very clean. 60 yards from Tiki bar with great live music, bar good and cold beer!!"

[](https://expedia.ca/Ramrod-Key-Hotels-Looe-Key-Reef-Resort.h4759500.Hotel-Information)

![Sugar Loaf Lodge](https://images.trvl-media.com/lodging/4000000/3920000/3918200/3918121/95d2903e_y.jpg)

### Sugar Loaf Lodge

10/10 Excellent

"…"

[](https://expedia.ca/Sugarloaf-Key-Hotels-Sugar-Loaf-Lodge.h3918121.Hotel-Information)

![Old Florida Style, wrap around porch, boat basin for dockage, open water](https://images.trvl-media.com/lodging/74000000/73240000/73238500/73238458/60b95cd9_y.jpg)

### Old Florida Style, wrap around porch, boat basin for dockage, open water

10/10 Excellent

"This property is fantastic and we highly recommend. Whether bringing your own boat, or renting one from next door from Dawn at Lower Keys Boat Rental - this is the perfect place to stay if you are planning to spend time on the water. There are pros and cons with every rental, so I have listed ours below:PROS:- Great location! You can find groceries and great food options very easily. This is a great spot to be secluded yet not too far off the beaten path. - Basin for Boating! The basin is wide enough and deep enough dock your boat regardless of winds or waters. - Easy Load-in to House! The house has a beautiful porch and just a few stairs to load your belongings into the house without having to lug them up a full story flight of stairs. - Pet Friendly! Our little guys loved staying at this property and it had plenty of yard for them to play and poop in. - Kitchen utensils are plentiful! Whether you are frying, boiling or steaming - you will have what you need here.CONS:- Lack of cleaning supplies and necessities: Be prepared to provide your own spray cleaning supplies as well as extra TP and papertowels. The provided cleaning supplies are lacking. - Boating to the Gulf: Unless you know the waters very well, getting to the Gulf from this location requires you to go out and around to one of the deeper channels to reach the Gulf. It is possible to get there from this location but unless you are confident in your path and the tides are right - don't chance it. "

[](https://expedia.ca/Little-Torch-Key-Hotels-Old-Florida-Style.h73238458.Hotel-Information)

![Canal front, dockage, 2 bedroom,  2 bath](https://images.trvl-media.com/lodging/62000000/61590000/61585200/61585151/4681bad1_y.jpg)

### Canal front, dockage, 2 bedroom, 2 bath

10/10 Excellent

"Neat and tidy………. Exactly as described and the same in the photos- Peaceful and relaxing! The kitchen was great and more importantly had everything equipped needed to cook, wash and eat! Bath towels also provided for guests. Back porch/dock area was cute and cozy- It was a very comfortable stay!"

[](https://expedia.ca/Summerland-Key-Hotels-Canal-Front.h61585151.Hotel-Information)

## Find out more about Summerland Key

## Summerland Key Vacation Homes information

| Number of reviews | 563 |
| --- | --- |
| Accommodation | 411 Vacation Homes |
| Lowest Price | CA $573 |
| Highest Price | CA $3,312 |

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-   [Resorts in Lower Keys](https://www.expedia.ca/Lower-Keys-Resort-Hotels.d553248621593965863-aaResortHotels.Travel-Guide-Accommodation)
-   [Aparthotels in Melody Key](https://www.expedia.ca/Melody-Key-Apart-Hotels.d553248635975749341-aaApartHotels.Travel-Guide-Accommodation)
-   [B&B in Melody Key](https://www.expedia.ca/Melody-Key-Bed-And-Breakfast.d553248635975749341-aaBedAndBreakfast.Travel-Guide-Accommodation)
-   [Cabin Rentals in Melody Key](https://www.expedia.ca/Melody-Key-Cabins.d553248635975749341-aaCabins.Travel-Guide-Accommodation)
-   [Condo Resorts in Melody Key](https://www.expedia.ca/Melody-Key-Condominium-Resort.d553248635975749341-aaCondominiumResort.Travel-Guide-Accommodation)
-   [Luxury Hotels in Melody Key](https://www.expedia.ca/Melody-Key-Hotels-Luxury-Hotel.0-0-d553248635975749341-tLuxuryHotel.Travel-Guide-Filter-Hotels)
-   [Melody Key Hotels](https://www.expedia.ca/Melody-Key-Hotels.d553248635975749341.Travel-Guide-Hotels)
-   [Resorts in Melody Key](https://www.expedia.ca/Melody-Key-Resort-Hotels.d553248635975749341-aaResortHotels.Travel-Guide-Accommodation)
-   [Villas in Melody Key](https://www.expedia.ca/Melody-Key-Villas.d553248635975749341-aaVillas.Travel-Guide-Accommodation)
-   [Middle Torch Key Hotels](https://www.expedia.ca/Middle-Torch-Key-Hotels.d553248635975870980.Travel-Guide-Hotels)
-   [Villas in Middle Torch Key](https://www.expedia.ca/Middle-Torch-Key-Villas.d553248635975870980-aaVillas.Travel-Guide-Accommodation)
-   [Beach Hotel Hotels in Ramrod Key](https://www.expedia.ca/Ramrod-Key-Hotels-Beach-Hotel.0-0-d6156102-tBeachHotel.Travel-Guide-Filter-Hotels)
-   [Oceanfront Hotels in Ramrod Key](https://www.expedia.ca/Ramrod-Key-Hotels-Oceanfront-Hotels.0-0-d6156102-tOceanfrontHotels.Travel-Guide-Filter-Hotels)
-   [Ramrod Key Hotels](https://www.expedia.ca/Ramrod-Key-Hotels.d6156102.Travel-Guide-Hotels)
-   [Resorts in Ramrod Key](https://www.expedia.ca/Ramrod-Key-Resort-Hotels.d6156102-aaResortHotels.Travel-Guide-Accommodation)

-   [Flights to Lower Keys](https://www.expedia.ca/Cheap-Flights-To-Lower-Keys.d553248621593965863.Travel-Guide-Flights)
-   [Flights to Melody Key](https://www.expedia.ca/Cheap-Flights-To-Melody-Key.d553248635975749341.Travel-Guide-Flights)
-   [Flights from New York to Ramrod Key](https://www.expedia.ca/lp/flights/178293/6156102/new-york-to-ramrod-key)
-   [Flights from Orlando to Cudjoe Key](https://www.expedia.ca/lp/flights/178294/3000430966/orlando-to-cudjoe-key)
-   [Flights from Melody Key](https://www.expedia.ca/lp/flights/553248635975749341/flights-from-melody-key)
-   [Flights from Ramrod Key](https://www.expedia.ca/lp/flights/6156102/flights-from-ramrod-key)

-   [Visit Cudjoe Key](https://www.expedia.ca/Cudjoe-Key.dx3000430966)
-   [Visit Little Torch Key](https://www.expedia.ca/Little-Torch-Key.dx177498)
-   [Lower Keys Vacations](https://www.expedia.ca/Lower-Keys.d553248621593965863.Destination-Travel-Guides)
-   [Visit Melody Key](https://www.expedia.ca/Melody-Key.dx553248635975749341)
-   [Visit Ramrod Key](https://www.expedia.ca/Ramrod-Key.dx6156102)

-   [Ada Rental Cars in Middle Torch Key](https://www.expedia.ca/ADA-Car-Rentals-In-Middle-Torch-Key.d553248635975870980-c1109.Car-Rental-Guide-Suppliers)
-   [Budget Israel Rental Cars in Melody Key](https://www.expedia.ca/Budget-Israel-Car-Rentals-In-Melody-Key.d553248635975749341-c1012.Car-Rental-Guide-Suppliers)
-   [Car rentals near Little Torch Key](https://www.expedia.ca/Car-Rentals-In-Little-Torch-Key.d177498.Car-Rental-Guide)
-   [Discount Quebec Rental Cars in Melody Key](https://www.expedia.ca/Discount-Quebec-Car-Rentals-In-Melody-Key.d553248635975749341-c1137.Car-Rental-Guide-Suppliers)
-   [Goldcar Key’n Go Rental Cars in Middle Torch Key](https://www.expedia.ca/Goldcar-Keyn-Go-Car-Rentals-In-Middle-Torch-Key.d553248635975870980-c1044.Car-Rental-Guide-Suppliers)
-   [Pickup Car Rentals in Lower Keys](https://www.expedia.ca/Pickup-Car-Rentals-In-Lower-Keys.d553248621593965863-tPickup.Car-Rental-Guide-Class)
-   [Rhodium Rental Cars in Middle Torch Key](https://www.expedia.ca/Rhodium-Car-Rentals-In-Middle-Torch-Key.d553248635975870980-c1121.Car-Rental-Guide-Suppliers)
-   [Wiber Rental Cars in Little Torch Key](https://www.expedia.ca/WIber-Car-Rentals-In-Little-Torch-Key.d177498-c1127.Car-Rental-Guide-Suppliers)
-   [Zezgo Rental Cars in Lower Keys](https://www.expedia.ca/ZezGo-Car-Rentals-In-Lower-Keys.d553248621593965863-c1122.Car-Rental-Guide-Suppliers)
-   [Zezgo Rental Cars in Ramrod Key](https://www.expedia.ca/ZezGo-Car-Rentals-In-Ramrod-Key.d6156102-c1122.Car-Rental-Guide-Suppliers)

-   [Cudjoe Key Vacation Rentals](https://www.expedia.ca/Cudjoe-Key-Vacation-Rentals.d3000430966.Travel-Guide-VacationRentals)
-   [Little Torch Key Vacation Rentals](https://www.expedia.ca/Little-Torch-Key-Vacation-Rentals.d177498.Travel-Guide-VacationRentals)

-   [Things to do in Cudjoe Key](https://www.expedia.ca/Things-To-Do-In-Cudjoe-Key.d3000430966.Travel-Guide-Activities)
-   [Things to do in Lower Keys](https://www.expedia.ca/Things-To-Do-In-Lower-Keys.d553248621593965863.Travel-Guide-Activities)
-   [Things to do in Ramrod Key](https://www.expedia.ca/Things-To-Do-In-Ramrod-Key.d6156102.Travel-Guide-Activities)

-   [Book Vacation Homes in Summerland Key on Expedia.com](https://www.expedia.com/Summerland-Key-Private-Vacation-Homes.d6177802-aaPrivateVacationHomes.Travel-Guide-Accommodation)