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Holiday rentals in Summerland Key

Find and book unique accommodation on Airbnb

Top-rated holiday rentals in Summerland Key

Guests agree: these stays are highly rated for location, cleanliness and more.

Superhost

Cottage in Cudjoe Key

4.92 out of 5 average rating, 130 reviews

ATLANTIS...Ocean Front Cottage Retreat!

ATLANTIS~An ocean front cottage retreat! Completely remodeled, direct ocean-front cottage offers everything you'll need for the perfect getaway. Boat dock (25ft), HD TVs, washer & dryer, S/S appliances & gas cooking! Complimentary kayaks & bikes plus access to all the Venture Out Residential Condominium Community amenities: heated pool, Jacuzzi, kiddie pool, tennis, basketball & bocce courts, ocean bay swimming area, marina w/fuel, boat ramps & wash station, and a convenience market on-site!

28 Dec – 4 Jan

€ 770 per night
Superhost

Tiny home in Big Pine Key

4.8 out of 5 average rating, 88 reviews

Breezy pines 28 foot 5th wheel trailer .

Central air,queen size bed in the bedroom,queen size futon in the living room, tv,stove,refrigerator,propane grill,wifi,and an outdoor dining table.Owner uses the outdoor storage shed for fishing purposes.Newly renovated vinyl floor.New carpet in the bedroom.New toilet installed.The water pressure has been fixed and is now perfect.One cup k cup machine.Mile marker 30.Take the north entrance.Take your first left.Take your second right.Bare right and lot 54 is the first trailer on the left.

16–23 Oct

€ 128 per night
Superhost

Home in Cudjoe Key

4.91 out of 5 average rating, 102 reviews

Sunrise Beach Escape

For your next vacation, come stay in this resort home, where you'll enjoy a cocktail at sunset alongside the Cudjoe bay overlooking the Atlantic Ocean. This beautiful and luxurious home is part of the Sunrise Beach Resort, an exclusive 11 home gated community overlooking the Atlantic Ocean & Cudjoe Bay. A community that is only 17 miles north of Key West. Make yourself at home in this tastefully decorated 1200 sq foot living space, which offers countless amenities such as kayaks and bikes.

6–13 Jul

€ 394 per night

Popular amenities for Summerland Key holiday rentals

Stay near Summerland Key's top sights

Square Grouper Bar and Grill47 locals recommend
Tonio's Seafood Shack & Tiki Bar14 locals recommend
Galley Grill19 locals recommend
My New Joint27 locals recommend
Murray's Market16 locals recommend
Cudjoe Sales Fishermen's Warehouse4 locals recommend

Other great holiday rentals in Summerland Key

Guest favourite

Home in Cudjoe Key

4.94 out of 5 average rating, 18 reviews

Conch Cabana in Paradise 23 miles outside Key West

7–14 Jun

€ 350 per night
Superhost

Home in Cudjoe Key

4.83 out of 5 average rating, 24 reviews

Keys Island Villa - Venture Out Home 354

19–26 Dec

€ 526 per night
Guest favourite

Campervan/Motorhome in Big Pine Key

4.91 out of 5 average rating, 34 reviews

Having fun in the lower Keys

31 Jul – 7 Aug

€ 180 per night
Guest favourite

Apartment in Key West

4.99 out of 5 average rating, 83 reviews

Hidden Beach Duplex, Best Place in Key West

2–9 Aug

€ 683 per night
Guest favourite

Cottage in Cudjoe Key

4.91 out of 5 average rating, 75 reviews

King Master, 2BR, 2BA, 35' Seawall, SUP, Kayaks

24 Feb – 3 Mar

€ 876 per night
Guest favourite

Home in Big Pine Key

4.89 out of 5 average rating, 62 reviews

Fishermen`s Paradise: Huge pool, 220-foot dock

8–15 Sep

€ 1,027 per night
Guest favourite

Campervan/Motorhome in Big Pine Key

4.94 out of 5 average rating, 34 reviews

Delightful 1 bedroom camper with pool

8–15 Jul

€ 188 per night
Superhost

Home in Cudjoe Key

4.84 out of 5 average rating, 37 reviews

Keys Cove

18–25 Jan

€ 398 per night
Guest favourite

Guest suite in Key Colony Beach

4.99 out of 5 average rating, 81 reviews

Turtle-By-The-Sea: the Best Deal in KCB!

3–10 May

€ 196 per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 5 reviews

Venture Out -Million Dollar Island Resort

23–30 Nov

€ 354 per night
Superhost

Home in Cudjoe Key

5.0 out of 5 average rating, 3 reviews

Latitudes-Ocean Front Pool

28 Sep – 5 Oct

€ 775 per night
Guest favourite

Holiday home in Cudjoe Key

5.0 out of 5 average rating, 30 reviews

Beautiful Cottage & Amenities in Gated Community

23–30 Aug

€ 379 per night

Quick stats about holiday rentals in Summerland Key

Total rentals

210 properties

Rentals with a pool

140 properties have a pool

Pet-friendly rentals

90 properties allow pets

Family-friendly rentals

180 properties are a good fit for families

Total number of reviews

3.3K reviews

Nightly prices starting at

€ 83 before taxes and fees

Destinations to explore

  1. Airbnb
  2. United States
  3. Florida
  4. Monroe County
  5. Summerland Key