Overseas highway in the Florida Keys taken by drone

Summerland Key Vacation Rentals

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Check prices for these dates

In two weeks
10 Jul - 12 Jul
In two months
21 Aug - 23 Aug
In three months
18 Sep - 20 Sep
In four months
16 Oct - 18 Oct

Our top choices for Summerland Key vacation rentals

Exterior detail

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

Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (5 reviews)
"Absolutely love it here… Randy is great to work with and always available. "
United States
Jeannine R.
The price is AED 807
AED 2,305 total
includes taxes & fees
29 Jun - 30 Jun
Charming 2-bedroom house with WiFi, AC in lovely Cudjoe Key
Terrace/patio

Waterfront Home

Waterfront Home
Cudjoe Key
8.8 out of 10, Excellent, (187 reviews)
"Clean and as described "
United States
Tim S.
The price is AED 735
AED 1,561 total
includes taxes & fees
9 Jul - 10 Jul
Waterfront Home
Outdoor dining

Cottage with Pool and Dockage, just minutes to Key West

Cottage with Pool and Dockage, just minutes to Key West
Cudjoe Key
9.4 out of 10, Exceptional, (171 reviews)
"Great place "
United States
David
The price is AED 909
AED 1,620 total
includes taxes & fees
15 Jul - 16 Jul
Cottage with Pool and Dockage, just minutes to Key West
A heated pool

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

Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Cudjoe 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."
United States
Cheryl V.
The price is AED 617
AED 2,086 total
includes taxes & fees
9 Jul - 10 Jul
Pet-Friendly Keys Cottage at Plankton's Palace - Pool, Patio & Gated Access
Exterior

Seabreeze Escape WF RV Lot 489

Seabreeze Escape WF RV Lot 489
Cudjoe Key
8.0 out of 10, Very Good, (1 review)
The price is AED 624
AED 1,107 total
includes taxes & fees
29 Jun - 30 Jun
Seabreeze Escape WF RV Lot 489
Exterior

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.4 out of 10, Exceptional, (109 reviews)
"Enjoyed our stay at Venture Out. Loved having the water view. We used the pool, bikes and kayaks. Owners were very responsive. House was clean. Would definitely stay again."
United States
Lindsey S.
The price is AED 657
AED 1,744 total
includes taxes & fees
29 Jun - 30 Jun
SAVE BIG $$ JUNE/JULY. WATERFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
A heated pool

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 West
Cudjoe 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 ."
United States
jim b.
The price is AED 675
AED 2,159 total
includes taxes & fees
13 Jul - 14 Jul
Updated 2BR/2BA Venture Out Home w/ Pool Access, Pet Friendly, Near Key West
Exterior

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS

SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Cudjoe Key
9.8 out of 10, Exceptional, (91 reviews)
"Great location, very clean, and a responsive host. We enjoyed our stay and highly recommended this spot!"
United States
David T.
The price is AED 841
AED 1,976 total
includes taxes & fees
29 Jun - 30 Jun
SAVE BIG $$ JUNE/JULY! OCEANFRONT 4 BIKES & 2-2 PERSON KAYAKS. KING & QUEEN BEDS
Beach

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West

Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Cudjoe Key
The price is AED 85
AED 1,370 total
includes taxes & fees
18 Jul - 19 Jul
Bright 2BR 2BA in Cudjoe Key| Sleeps 6 | WiFi | Washer Dryer | Near Water & Key West
Beach

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West

Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Cudjoe Key
The price is AED 424
AED 1,844 total
includes taxes & fees
29 Jun - 30 Jun
Affordable Dog Friendly Keys Retreat in Venture Out Near Key West
Fridge, microwave, oven, stovetop

Kelly's Kabin - Adorable Private Summerland Key Cottage

Kelly's Kabin - Adorable Private Summerland Key Cottage
Summerland Key
9.8 out of 10, Exceptional, (124 reviews)
"House was very clean and in close proximity to Key West, Marathon, and Big Pine Key."
United States
Sharon L.
The price is AED 826
AED 2,001 total
includes taxes & fees
12 Jul - 13 Jul
Kelly's Kabin - Adorable Private Summerland Key Cottage
Property grounds

Endless Ocean Views - RV589

Endless Ocean Views - RV589
Cudjoe Key
The price is AED 716
AED 1,225 total
includes taxes & fees
29 Jun - 30 Jun
Endless Ocean Views - RV589
Property grounds

Cudjoe Cottages, swimming pool, just 20 miles from Key West

Cudjoe Cottages, swimming pool, just 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (160 reviews)
"This was our second stay here and just as we remembered. It was clean and we had everything we needed. Would recommend it for visiting Key West as its only a 30 minute drive in."
United States
John S.
The price is AED 992
AED 2,188 total
includes taxes & fees
29 Jun - 30 Jun
Cudjoe Cottages, swimming pool, just 20 miles from Key West
Beach

Canalfront Keys Home - Dock for 35' Boat, Large Porch, Big Yard & Quick Access to Open Water

Canalfront Keys Home - Dock for 35' Boat, Large Porch, Big Yard & Quick Access to Open Water
Cudjoe Key
The price is AED 964
AED 2,429 total
includes taxes & fees
29 Jun - 30 Jun
Canalfront Keys Home - Dock for 35' Boat, Large Porch, Big Yard & Quick Access to Open Water
A heated pool

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West

Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Cudjoe Key
8.8 out of 10, Excellent, (10 reviews)
"We loved our stayed and booked again for next year. Its in our price range, plenty of space and we were all so comfortable. Its our favorite house we have rented in the area and hope to be able to continue to enjoy it years to come. "
United States
Alisa M.
The price is AED 694
AED 2,169 total
includes taxes & fees
6 Jul - 7 Jul
Blue Lobster Lodge #543 Open Coastal Retreat with Pool Near Key West
Terrace/patio

Starlight Serenity - Hideaway with Stunning Views

Starlight Serenity - Hideaway with Stunning Views
Summerland Key
10.0 out of 10, Exceptional, (1 review)
"This place was everything we needed. The location was the perfect combination of secluded but with accessibility to Marathon and Key West. The house had everything we needed. We loved the appliances, the bed, the shower and the wrap-around porch with the swing. And the people managing the property made our visit the best experience from booking to departure. Will book again!"
United States
Tom H.
The price is AED 790
AED 2,275 total
includes taxes & fees
1 Jul - 2 Jul
Starlight Serenity - Hideaway with Stunning Views
Beach

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

Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Cudjoe Key
9.4 out of 10, Exceptional, (3 reviews)
"Stayed with family and good location for family vacations. "
United States
Phani U.
The price is AED 771
AED 2,282 total
includes taxes & fees
29 Jun - 30 Jun
Florida Keys Canal-Front 2BR/2BA w/ 35' Seawall, Dock & Spacious Comfort
Exterior

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West

Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
Cudjoe Key
8.8 out of 10, Excellent, (173 reviews)
"Great location with a great staff. The Bug House is very spacious and clean. I would recommend it as a great place to stay and relax with family. "
United States
Phillip
The price is AED 1,157
AED 2,400 total
includes taxes & fees
5 Jul - 6 Jul
Direct Oceanfront-Atlantic Side-Dockage-Pool and 20 miles from Key West
A heated pool

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key

Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
Cudjoe Key
10.0 out of 10, Exceptional, (3 reviews)
"Pool area was nice but only visited it once as so much to see and do!"
United States
Karen
The price is AED 868
AED 2,405 total
includes taxes & fees
29 Jun - 30 Jun
Waterfront 2BR/2BA | 35' Seawall for 32' Boat | Beautiful Sunrises on Cudjoe Key
A heated pool

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors

Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
Cudjoe Key
8.0 out of 10, Very Good, (1 review)
The price is AED 771
AED 2,282 total
includes taxes & fees
9 Jul - 10 Jul
Waterfront Getaway with 23' Seawall, Boat Access, Outdoor Dining & Cozy Interiors
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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Top Summerland Key Hotel Reviews

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

10/10 Excellent
"Property was great with a perfect location. The host was as very responsive with any of our questions throughout the week. Great place and would definitely stay again."
Eric W. 7-night trip
Posted 1 day ago
Waterfront 2BR Home w/ Dock + Golf Cart, Open Water Views in Venture Out

Frequently asked questions

Can I find vacation rentals in Summerland Key?

Yes, you can find vacation rentals close to top local attractions in Summerland Key, or you can choose a secluded option if you want a relaxing place to stay.

What's the top vacation rental in Summerland Key?

Sugarloaf Key RV Resort & Cottages: This Summerland Key vacation home rental is located near a metro station and offers an outdoor pool, air-conditioning, and free WiFi to help you feel perfectly comfortable in your new surroundings. This vacation rental also comes with free parking to give you added peace of mind. Other favorite homes for rent in Summerland Key are Old Florida Style, wrap around porch, boat basin for dockage, open water and Oceanside in the FL Keys Free Kayaks Bikes Pool & Hot Tub Tennis & Pickle ball.

How many vacation rentals are there in Summerland Key?

Choose from 473 Expedia vacation rentals in Summerland Key for a memorable vacation.

What can I see and do in Summerland Key?

Florida Keys Beaches and Upper Sugarloaf Key are a couple of lovely local spots to get outside and enjoy nature. Sugarloaf Beach and Crab Key are other places to visit while you're in town.

What are vacation rentals like in Summerland Key?

Vacation rentals are private accommodations you can reserve for a few days or a quick weekend in Summerland Key. Vacation rentals feature extras such as laundry facilities and kitchens so your stay will be comfortable. If you're concerned about a clean environment, a vacation rental can provide a sense of privacy away from shared hotel elevators and busy reception areas while still allowing you to travel. You'll also get more space in a vacation rental than in a traditional hotel, which makes a vacation rental a great choice for family trips.