Summerland Key Vacation Rentals
Change your mindBook hotels with free cancellation
Be pickySearch almost a million properties worldwide
Check prices for these dates
In two weeks
In two months
In three months
In four months
Our top choices for Summerland Key vacation homes
1. SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
SAVE BIG $$$ SEPT/OCT. OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDSCudjoe Key
9.8 out of 10, Exceptional, (96 reviews)
"Great location, wonderful hosts!"
Blue Mountain Footwear F.
The price is CA $208
CA $604 total
includes taxes & fees
Sep 27 - Sep 28
2. Kelly's Kabin - Adorable Private Summerland Key Cottage
Kelly's Kabin - Adorable Private Summerland Key CottageSummerland Key
9.8 out of 10, Exceptional, (128 reviews)
"Very nice place. Centrally located near good restaurants, markets, etc.. Pet friendly which worked for us. Nice long walking trail behind cottage."
John B.
The price is CA $271
CA $704 total
includes taxes & fees
Sep 19 - Sep 20
3. SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
SAVE BIG $$$ SEPT/OCT. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDSCudjoe Key
9.4 out of 10, Exceptional, (111 reviews)
"Our family had an amazing time staying here! Our hosts were quick to answer any questions we had and the house was clean and fully stocked with everything you might need. Our favorite part was being able to sit out on the deck by the canal and see all the marine wildlife. We even had a little family of manatees hang out for awhile. Definitely would recommend staying here!"
Mckayla S.
The price is CA $180
CA $573 total
includes taxes & fees
Sep 21 - Sep 22
4. Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated AccessCudjoe Key
10.0 out of 10, Exceptional, (1 review)
"Excellent location - clean, quiet, well-kept community. Boat launch was key for us. Pool and beach looked very nice, but we didn't use. The unit is as described and has a nice patio out back that we used every day."
Cheryl V.
The price is CA $219
CA $637 total
includes taxes & fees
Sep 19 - Sep 20
5. Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe KeyCudjoe Key
9.8 out of 10, Exceptional, (6 reviews)
"Property was perfectly located and very clean and comfortable."
Kiara
The price is CA $258
CA $813 total
includes taxes & fees
Sep 21 - Sep 22
6. Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key WestCudjoe Key
8.0 out of 10, Very good, (3 reviews)
" Great 2 bedroom home in a lovely vacation community . We enjoyed the 2 recliners to relax after a full day of exploring as well as in the morning with our coffee. The screened in patio was a nice perk as well . At check in , a calendar of events was provided and the staff were friendly and helpful. FYI : We enjoyed a gorgeous sunrise right by the beach near the pool ."
jim b.
The price is CA $241
CA $797 total
includes taxes & fees
Sep 18 - Sep 19
7. Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart Option
Canal Front Retreat w/ Ocean Views, 35' Dock & Golf Cart OptionCudjoe Key
9.4 out of 10, Exceptional, (18 reviews)
"Our family had an amazing vacation! We love the house and hope to come back!! "
Tammy G.
The price is CA $278
CA $714 total
includes taxes & fees
Sep 21 - Sep 22
8. Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious ComfortCudjoe Key
9.6 out of 10, Exceptional, (5 reviews)
"Stayed with family and good location for family vacations. "
Phani U.
The price is CA $292
CA $862 total
includes taxes & fees
Sep 18 - Sep 19
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.
Find vacation rentals that suit your style
Cottages
Private vacation homes
Save an average of 15% on thousands of hotels when you're signed in
Top Summerland Key Hotel Reviews
Sugar Loaf Lodge
10/10 Excellent
Find out more about Summerland Key
Summerland Key Vacation Homes information
Number of reviews | 336 |
|---|---|
Accommodation | 384 Vacation Homes |
Lowest Price | CA $573 |
Highest Price | CA $886 |
Explore a world of travel with Expedia
- Cottages in Key West
- Condo Rentals in Marathon
- Houseboats in Cow Key
- Aparthotels in Marathon
- Resorts in Big Pine Key
- Hotel Wedding Venues Hotels in Cudjoe Key
- Old Florida Style
- Slice of Paradise
- Apartments in Sugarloaf Key
- Adults Only Resorts & in Eden Pines
- Cruise Ships in Key West
- Barnacle Resort
- Beach Hotel Hotels in Key West
- Guest Houses in Key West
- Lodges in Key Colony Beach
- Cheap Hotels in Big Pine Key
- Cabin Rentals in Marathon
- Cheap Hotels in Key West
- 5 Star Hotels in Big Pine Key
- B&B in Key West
- Cabin Rentals in Boca Chica Key
- Beach Hotel Hotels in Cutthroat Harbor Estates
- Villas in Key West
- Vacation Homes in Monroe County
- Villas in Key Haven
- Villas in Summerland Key
- Summerland Key Hotels
- Houseboats in Marathon
- Tree Top Paradise
- Hilton Hotels in Big Pine Key
- Palm COTTAGE
- Cabin Rentals in Key West
- Motels in Key Haven
- Cottages in Marathon
- Cabin Rentals in No Name Key
- Hotel Wedding Venues Hotels in Big Pine Key
- Beautiful Family
- Resorts in Key West
- Resorts in Cudjoe Key
- Condo Rentals in Key West
- Save BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2
- Condo Resorts in Key West
- Vacation Homes in Key West
- Apartments in Key West
- All Inclusive Resorts and in Key West
- Deer Run Bed & Breakfast
- Houseboats in Key West
- Ed & Ellen's Lodging Big Pine Key
- Key West Hotels
- Motels in Key West
- Villa Jekjak
- Big Pine Key Hotels
- Motels in Marathon
- Beachfront 3B/3B Fishing Oasis
- Flights to Big Pine Key
- Flights from Fort Lauderdale (FLL) to Key West (EYW)
- Flights from Ramrod Key
- Flights to Key West
- Flights from Miami (MIA) to Key West (EYW)
- Flights from Ottawa (YOW) to Key West (EYW)
- Flights from Toronto (YYZ) to Key West (EYW)
- Flights to Summerland Key
- Flights from Melody Key
- Flights from Montreal (YUL) to Key West (EYW)
- Flights from Detroit (DTW) to Key West (EYW)
- Flights to Melody Key
- Flights from Summerland Key
- Flights from Orlando (MCO) to Key West (EYW)
- Key West Vacations
- Visit Ramrod Key
- Visit Little Torch Key
- All inclusive Vacation Packages Sugarloaf Key
- Visit Cudjoe Key
- Visit Sugarloaf Key
- All inclusive Vacation Packages Key West
- Sombrero Beach
- Visit Big Pine Key
- Beach Vacation Packages Cudjoe Key
- Visit Big Torch Key
- Visit Doctor's Arm
- Visit Summerland Key