Title: Summerland Key Vacation Rentals from CA $518: Short-Term Rentals for 2026 | 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)[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)

![A783WA Newspaper Vending Machines unbelievable view infinity endless water road vast waterfront America Americas beach beaches](https://images.trvl-media.com/place/6177802/c883ce32-6f25-4ec1-b4af-7d73d0d15242.jpg?impolicy=fcrop&w=1200&h=500&q=medium)

# Summerland Key Vacation Rentals

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## Check prices for these dates

In two weeks

[Jan 9 - Jan 11](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2026-01-09&endDate=2026-01-11&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[Feb 20 - Feb 22](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2026-02-20&endDate=2026-02-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[Mar 20 - Mar 22](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2026-03-20&endDate=2026-03-22&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[Apr 17 - Apr 19](https://www.expedia.ca/Hotel-Search?regionId=6177802&startDate=2026-04-17&endDate=2026-04-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Summerland Key vacation rentals

![Beach nearby](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/13a191dd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/00dc7121.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/cd44e6df.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/17d08c7d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h74236945.Hotel-Information)

8.2/10

Very good

(53)

"Great area. Quiet and comfortable "

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

nancy c.

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h74236945.Hotel-Information)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/88788395.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/2b4d6024.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/5ff4b852.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![2 bedrooms, iron/ironing board, WiFi, bed sheets](https://images.trvl-media.com/lodging/84000000/83450000/83440800/83440767/d142accd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Island-Oasis-YOUR-Paradise-Awaits-In-Venture-Out-Resort.h83440767.Hotel-Information)

9.6/10

Exceptional

(12)

"The owners were fantastic to deal with and the house was great. "

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

Anonymous traveller

[](https://www.expedia.ca/Cudjoe-Key-Hotels-Island-Oasis-YOUR-Paradise-Awaits-In-Venture-Out-Resort.h83440767.Hotel-Information)

![Miscellaneous](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/49b733bd.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/bc83e7d9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/00d423f8.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/34000000/33570000/33566300/33566283/f3c522ff.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

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

9.0/10

Wonderful

(160)

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

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

Terry

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

![Beach](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/ef0fcc3f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/4231ea78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/f9f1343b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool](https://images.trvl-media.com/lodging/34000000/33570000/33564800/33564734/29403089.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Private-Oceanfront-Cottage-With-Dockage.h33564734.Hotel-Information)

8.6/10

Excellent

(164)

"Beautiful serene, location, located close enough to Key West and also nice restaurants in the area and close to Bahia Honda State Park, which was beautiful and the key deer areas."

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

Andrea S.

CA $308

CA $518 total

includes taxes & fees

Jan 19 - Jan 20, 2026

[](https://www.expedia.ca/Summerland-Key-Hotels-Private-Oceanfront-Cottage-With-Dockage.h33564734.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/ab69be49.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House](https://images.trvl-media.com/lodging/112000000/111880000/111873000/111872953/ea10b4e4.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)

### Vacation Home in Summerland Key

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

CA $557

CA $1,084 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

![TV](https://images.trvl-media.com/lodging/78000000/77070000/77064100/77064022/b5a934e4.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)

### Vacation Home in Upper Sugarloaf Key

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

9.6/10

Exceptional

(8)

"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 $1,880

CA $3,151 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![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)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/33000000/32670000/32660400/32660303/f111b153.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)

### Vacation Home in Cudjoe Key

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

9.4/10

Exceptional

(101)

"Great location. "

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

Davian k.

CA $409

CA $834 total

includes taxes & fees

Jan 10 - Jan 11, 2026

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

![Terrace/patio](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/548e5f5d.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/faef98d6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/752e4335.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/106000000/105240000/105238300/105238265/6b5c5ac3.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Camping in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Seabreeze-Escape-WF-RV-Lot-489.h105238265.Hotel-Information)

8.0/10

Very good

(1)

CA $233

CA $411 total

includes taxes & fees

Dec 29 - Dec 30

[](https://www.expedia.ca/Summerland-Key-Hotels-Seabreeze-Escape-WF-RV-Lot-489.h105238265.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)

### Vacation Home in Cudjoe Key

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

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 $409

CA $835 total

includes taxes & fees

Jan 18 - Jan 19, 2026

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

![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/ce42ac53.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor dining](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/4bda4a1b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Marina](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/c4e05ae6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Property grounds](https://images.trvl-media.com/lodging/105000000/104880000/104875300/104875207/2f62f857.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Camping in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.Hotel-Information)

CA $232

CA $408 total

includes taxes & fees

Dec 27 - Dec 28

[](https://www.expedia.ca/Summerland-Key-Hotels-Endless-Summer-Hideaway-Lot-181.h104875207.Hotel-Information)

![A heated pool](https://images.trvl-media.com/lodging/113000000/112980000/112976000/112975923/81fafea6.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/113000000/112980000/112976000/112975923/w2499h1666x1y1-83af97d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Beach](https://images.trvl-media.com/lodging/113000000/112980000/112976000/112975923/6fd19ec9.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/113000000/112980000/112976000/112975923/w2499h1666x1y1-6358dbd2.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Mobile Home in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Saltwater-Serenity-392-Ocean-Views-On-Cudjoe-Key.h112975923.Hotel-Information)

10/10

Exceptional

(8)

"The property was really nice and super clean! Easy access and quiet neighborhood."

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

VANESSA T.

CA $395

CA $982 total

includes taxes & fees

Jan 4 - Jan 5, 2026

[](https://www.expedia.ca/Summerland-Key-Hotels-Saltwater-Serenity-392-Ocean-Views-On-Cudjoe-Key.h112975923.Hotel-Information)

![Swim-up bar](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/17e19347.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Villa, Ocean View | Garden view](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w1153h1530x0y2-2909ca24.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Deluxe Villa, Ocean View](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2298h1530x0y2-8c5d1221.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Porch](https://images.trvl-media.com/lodging/112000000/111540000/111535500/111535402/w2298h1532x0y2-24d28430.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Villa in Summerland Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information)

10/10

Exceptional

(1)

"We were here for a night and it was great. A nice rustic feel on a big property, with good view. "

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

Preetam

CA $770

CA $1,405 total

includes taxes & fees

Jan 16 - Jan 17, 2026

[](https://www.expedia.ca/Summerland-Key-Hotels-Atlantic-View-Luxury-Villa-With-Pool.h111535402.Hotel-Information)

![Pool](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/e8302fa4.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/317baf78.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/ae1e02d5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/90000000/89820000/89810800/89810800/3ecf1ac7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Upper Sugarloaf Key

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-BUNGALOWS-AT-SUGARLOAF-BEACH-THE-LIGHTHOUSE.h89810800.Hotel-Information)

9.6/10

Exceptional

(11)

"Thank you for our wonderful stay at this beautiful property - everything was perfect - Peter"

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

Peter Q.

CA $1,505

CA $2,413 total

includes taxes & fees

Dec 28 - Dec 29

[](https://www.expedia.ca/Sugarloaf-Key-Hotels-BUNGALOWS-AT-SUGARLOAF-BEACH-THE-LIGHTHOUSE.h89810800.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/117000000/116670000/116667100/116667062/3a5c1145.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)

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

### Vacation Home in Cudjoe Key

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

CA $287

CA $841 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

![Beach nearby](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/792acc55.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Outdoor pool, a heated pool](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/1387427b.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Interior](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/3bedcb76.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/76000000/75870000/75862800/75862770/4b744822.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h75862770.Hotel-Information)

8.6/10

Excellent

(75)

"Place was everything we needed, would definitely stay again "

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

James h.

[](https://www.expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h75862770.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)

![Fridge, microwave, stovetop, dishwasher](https://images.trvl-media.com/lodging/39000000/38420000/38413600/38413504/w1719h1144x6y0-9b572dbd.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)

### Vacation Home in Summerland Key

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

8.8/10

Excellent

(65)

"Excellent secluded location but near everything Thanks!!!!!"

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

Gary D.

CA $737

CA $1,799 total

includes taxes & fees

Jan 7 - Jan 8, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/9d9f7a21.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/facc5471.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV, offices](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/dcb46088.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Terrace/patio](https://images.trvl-media.com/lodging/112000000/111880000/111873800/111873736/587f6dd1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Summerland Key

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

CA $397

CA $959 total

includes taxes & fees

Jan 6 - Jan 7, 2026

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

![Fridge, microwave, oven, stovetop](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/fadc9b44.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![TV](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/61e6cf8f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Pool](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/133c6194.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Exterior detail](https://images.trvl-media.com/lodging/34000000/33550000/33548300/33548243/515ffa6f.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Cottage in Cudjoe Key

[](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.Hotel-Information)

8.6/10

Excellent

(120)

"Jennifer was very nice and accommodating."

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

Randy G.

[](https://www.expedia.ca/Summerland-Key-Hotels-Charming-Cottages.h33548243.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)

![Exterior](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/7f2df60c.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)

![Beach](https://images.trvl-media.com/lodging/122000000/121320000/121310600/121310574/c2c1b6c7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cudjoe Key

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

8.0/10

Very good

(1)

"It was a short trip but we enjoyed our stay! "

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

Jennifer S.

CA $431

CA $1,002 total

includes taxes & fees

Jan 2 - Jan 3, 2026

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

![Property grounds](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/b38fa56b.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)

![Dining](https://images.trvl-media.com/lodging/110000000/109800000/109794900/109794896/04d12b41.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Vacation Home in Cudjoe Key

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

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 $395

CA $982 total

includes taxes & fees

Jan 4 - Jan 5, 2026

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

[View all properties](https://expedia.ca/Hotel-Search?startDate=2026-01-08&endDate=2026-01-09&regionId=6177802&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find vacation rentals that suit your style

Private vacation homes

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Apartments

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Condos

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Villas

[](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America&regionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=VILLA)

Houseboats

[](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America&regionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=HOUSE_BOAT)

Cottages

[](https://www.expedia.ca/Hotel-Search?destination=Summerland+Key%2C+Florida%2C+United+States+of+America&regionId=6177802&latLong=24.661335%2C-81.444847&adults=2&startDate=2026-03-25&d1=2026-03-25&endDate=2026-03-28&d2=2026-03-28&lodging=COTTAGE)

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## Top Summerland Key Hotel Reviews

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

### Sugar Loaf Lodge

10/10 Excellent

"Staff was wonderful. Room is sweet and on pretty piece of water. Aging property, but well kept. Quiet, clean, good shower, comfy beds. Quick trip to key west. Great deal for the money. Very happy this is where we landed."

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

"Staff very polite and accommodating. "

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

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

### Parmer's Resort

10/10 Excellent

"Beautiful and relaxing "

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

"Nice appartement, very clean place, with amazing shower. The site and the pool was extra clean and the staff was cool too."

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

![COCONUT TELEGRAPH ~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!](https://images.trvl-media.com/lodging/100000000/99880000/99870700/99870679/60738f85_y.jpg)

### COCONUT TELEGRAPH \~ Waterfront 2 BR/2Ba in Cudjoe Key w/ Dockage & Parking!

10/10 Excellent

"Great place!"

[](https://expedia.ca/Summerland-Key-Hotels-COCONUT-TELEGRAPH-Waterfront-2-BR2Ba-In-Cudjoe-Key-W-Dockage-Parking.h99870679.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

"Very nice"

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

"Loved the location, good communication!"

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

![Cottage with Pool  and Boat Dockage just minutes to Key West!](https://images.trvl-media.com/lodging/34000000/33920000/33912100/33912031/2c7b5ad1_y.jpg)

### Cottage with Pool and Boat Dockage just minutes to Key West!

10/10 Excellent

"The host was welcoming, helpful and very responsive. It was great to work with her and we thoroughly enjoyed our stay in her place. The amenities were great too -- boat dockage, pool, washer & dryer and the place had everything you would need. We will definitely stay here again! Thank you for sharing your rental with us. "

[](https://expedia.ca/Summerland-Key-Hotels-Cottage-With-Pool-And-Boat-Dockage-Just-Minutes-To-Key-West.h33912031.Hotel-Information)

![Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West](https://images.trvl-media.com/lodging/75000000/74240000/74237000/74236945/13a191dd_y.jpg)

### Old Florida Style, Dockage, Swimming Pool (shared), just 20 miles from Key West

10/10 Excellent

"Beautiful location & host are very accommodating and responsive. Will be back "

[](https://expedia.ca/Summerland-Key-Hotels-Old-Florida-Style.h74236945.Hotel-Information)

## Find out more about Summerland Key

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.  
  
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Summerland Key. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.   
  
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.   

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- [Vacation Homes in Summerland Key ](https://expedia.ca/Summerland-Key-Private-Vacation-Homes.d6177802-aaPrivateVacationHomes.Travel-Guide-Accommodation)
- [Cottages in Summerland Key ](https://expedia.ca/Summerland-Key-Cottages.d6177802-aaCottages.Travel-Guide-Accommodation)
- [RV Parks in Summerland Key ](https://expedia.ca/Summerland-Key-RV-Parks.d6177802-aaRVParks.Travel-Guide-Accommodation)
- [Villas in Summerland Key ](https://expedia.ca/Summerland-Key-Villas.d6177802-aaVillas.Travel-Guide-Accommodation)
- [Resorts in Summerland Key ](https://expedia.ca/Summerland-Key-Resort-Hotels.d6177802-aaResortHotels.Travel-Guide-Accommodation)
- [Motels in Summerland Key ](https://expedia.ca/Summerland-Key-Motels.d6177802-aaMotels.Travel-Guide-Accommodation)
- [Condo Rentals in Summerland Key ](https://expedia.ca/Summerland-Key-Condos.d6177802-aaCondos.Travel-Guide-Accommodation)

## Frequently asked questions

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