House vacation rentals in Summerland Key
Find and book unique houses on Airbnb
Top-rated house rentals in Summerland Key
Guests agree: these houses are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Summerland Key house rentals
House rentals with a pool
Home in Cudjoe Key
5.0 out of 5 average rating, 7 reviewsVenture Out- Million Dollar Island Resort
Dec 7 – 14
Home in Cudjoe Key
4.82 out of 5 average rating, 49 reviewsSpanish Queen @Venture Out
Jan 7 – 14
Home in Cudjoe Key
4.86 out of 5 average rating, 28 reviewsKeys Island Villa - Venture Out Home 354
Sep 26 – Oct 3
Home in Cudjoe Key
4.88 out of 5 average rating, 73 reviewsIsland Oasis ~ YOUR Paradise Awaits!
Mar 22 – 29
Home in Cudjoe Key
4.95 out of 5 average rating, 19 reviewsConch Cabana in Paradise 23 miles outside Key West
Apr 8 – 15
Home in Cudjoe Key
4.82 out of 5 average rating, 11 reviewsRise-N-Shine
Mar 23 – 30
Home in Cudjoe Key
5.0 out of 5 average rating, 12 reviewsSea Turtle Cove
Oct 13 – 20
Home in Big Pine Key
4.89 out of 5 average rating, 63 reviewsFishermen`s Paradise
Dec 4 – 11
Weekly house rentals
Home in Marathon
4.97 out of 5 average rating, 35 reviewsThe Gulf Cottage at Marathon Key
Jul 4 – 11
Home in Marathon
5.0 out of 5 average rating, 10 reviewsCanal Front, Boat Dock, Updated!
Aug 11 – 18
Home in Marathon
4.94 out of 5 average rating, 35 reviewsGorgeous Ocean View Home!
Apr 4 – 11
Home in Cudjoe Key
4.92 out of 5 average rating, 12 reviewsWaterfront 35’ Dock,80’ pool,20 min Key West
Dec 21 – 28
Home in Marathon
5.0 out of 5 average rating, 24 reviewsCoral Lagoon #23- Private Home with Boat Slip
Nov 3 – 10
Home in Cudjoe Key
4.89 out of 5 average rating, 28 reviewsCozy 2 br/2 bath home in Cudjoe
Oct 20 – 27
Home in Marathon
4.96 out of 5 average rating, 84 reviewsAngler’s Eden
Feb 3 – 10
Home in Cudjoe Key
4.88 out of 5 average rating, 17 reviewsPelican's Roost, Waterfront comfort at Venture Out
Dec 4 – 11
Private house rentals
Home in Cudjoe Key
4.83 out of 5 average rating, 6 reviewsSailfish Haven
Sep 3 – 10
Home in Cudjoe Key
4.78 out of 5 average rating, 9 reviewsCuddie Cottage: Open Water Views, Pool/Hot Tub!
Jul 3 – 10
Home in Marathon
4.97 out of 5 average rating, 59 reviewsPrivate 174ft Dock, Boat Launch, Sombrero Beach
Feb 23 – Mar 2
Home in Key Colony Beach
5.0 out of 5 average rating, 96 reviewsABeachBungalow-60’dock w/ access to pool and beach
Apr 19 – 26
Home in Marathon
4.97 out of 5 average rating, 36 reviewsWaterfront Private Home w/Pool-Family&Pet Friendly
Oct 6 – 13
Home in Marathon
5.0 out of 5 average rating, 17 reviewsGrouper Getaway @ Ocean Isles Fishing Village
Jan 14 – 21
Home in Marathon
5.0 out of 5 average rating, 17 reviewsGuest Fav I Hot Tub | Ping Pong I 17’ Boat
Nov 21 – 28
Home in Marathon
4.9 out of 5 average rating, 39 reviewsMarathon Beach House
Oct 3 – 10
Quick stats about house rentals in Summerland Key
Total rentals
170 properties
Rentals with a pool
100 properties have a pool
Pet-friendly rentals
60 properties allow pets
Family-friendly rentals
150 properties are a good fit for families
Total number of reviews
2.5K reviews
Nightly prices starting at
$130 before taxes and fees
Destinations to explore
- Key West Vacation rentals
- Varadero Vacation rentals
- Naples Vacation rentals
- Miami Vacation rentals
- Miami Beach Vacation rentals
- Havana Vacation rentals
- Fort Lauderdale Vacation rentals
- Boca Raton Vacation rentals
- West Palm Beach Vacation rentals
- Sarasota Vacation rentals
- Anna Maria Island Vacation rentals
- Tampa Vacation rentals
- Guesthouse rentals United States
- Townhouse rentals United States
- House rentals United States
- Earth house rentals United States
- Lighthouse rentals United States
- Townhouse rentals Florida
- Beach house rentals Florida
- Lakehouse rentals Florida
- Tiny house rentals Florida
- Guesthouse rentals Florida
- House rentals Florida
- Beach house rentals Key West
- Townhouse rentals Key West
- House rentals Key West
- House rentals Florida Keys
- Tiny house rentals Florida Keys
- Beach house rentals Florida Keys
- Townhouse rentals Florida Keys
- Guesthouse rentals Florida Keys
- House rentals Marco Island
- Beach house rentals Marco Island
- Rentals with a hot tub Summerland Key
- Rentals with a washer and dryer Summerland Key
- Rentals with a kayak Summerland Key
- Rentals with a patio Summerland Key
- Rentals with beach access Summerland Key
- Rentals with pools Summerland Key
- Family-friendly rentals Summerland Key
- Pet-friendly rentals Summerland Key
- Waterfront rentals Summerland Key
- Kid-friendly rentals Summerland Key
- Monthly Rentals Summerland Key
- Rentals with outdoor seating Summerland Key
- Guesthouse rentals Monroe County
- Tiny house rentals Monroe County
- Townhouse rentals Monroe County
- House rentals Monroe County
- Cabins United States
- Treehouses United States
- Glamping United States
- Tiny Houses United States
- Beach Houses United States
- Campers and RVs United States
- Lakehouses United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- Family travel hub Tips and inspiration
- Family budget travel Get there for less
- Vacation ideas for any budget Make it special without making it spendy
- Travel Europe on a budget How to take the kids to Europe for less
- Outdoor adventure Explore nature with the family
- Bucket list national parks Must-see parks for family travel
- Kid-friendly state parks Check out these family-friendly hikes